Dimethylformamide → 2,3-Dimethoxybenzoyl chloride

HRID 2119321Notes

Reaction equation

HRID 2119321 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](O)=[O:6].CN(C=O)C.C(Cl)(=O)C([Cl:22])=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([Cl:22])=[O:6]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 152042,3-Dimethoxybenzoic acidHCID 65578Oxalyl chloride

Product 1

HCID 27583922,3-Dimethoxybenzoyl chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,3-dimethoxybenzoic acid (10.9781 mmol, 2.0 g) in CH2Cl2 (20 mL) with a drop of DMF, was added oxalyl chloride (10.9781 mmol, 957.702:l) dropwise at RT After 2 hrs the reaction mixture was concentrated in vacuo to afford 2,3-dimethoxybenzoyl chloride (1.9 g, 90%): 1H NMR (CDCl3, 300 MHz, ppm): 7.52 (m, 1H), 7.12 (d, 2H), 3.89 (s, 3H), 3.88 (s, 3H).

Workup

  1. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-8e07124c9dd84b38b4541a0aa64e6ac8
Source dataset
uspto-grants-2004_02
Patent number
US06686350B1

Reaction notes

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